Pint-sized player Pookey Wigington is now a towering figure in comedy

This story appeared in the September 29, 2014, issue of Sports Illustrated. Subscribe to the magazine here.

Kevin Hart has risen to the top of the comedy world, but you wouldn’t know it from listening to many of his stand-up routines. Oh, sure, they’re hilarious. But he is the master of jokes about Kevin Hart; he can have audiences rolling at stories about his own mistakes and flaws.

“Lying ruined my marriage,” he says.

“That’s a lie. I cheated.”

Then there is his routine about “staying in your financial lane,” and the temptations that cause a man to spend more than he has.

“Athletes will mess your life up, man,” Hart says. “They will. Dwyane Wade is a good friend of mine. I can’t hang out with Dwyane no more. Dwyane tried to f--- my life up. Dwyane tried to make me buy a boat. I don’t even have a f------ house!”

Wiginton reached 1989 NCAA final with Seton Hall.

Courtesy of Seton Hall

​It’s funny and maybe true, but one athlete has helped Hart stay in his financial lane.

Actually, 48-year-old Pookey Wigington has done more than that. A former 5' 3" backup point guard for Seton Hall -- Hart has an inch on him -- Wigington averaged 1.7 points in two seasons and played in the 1989 national-title game for the Pirates, a one-point overtime loss to Michigan. And the smallest basketball player in Big East history would go on to do even bigger things.

Leland WigingtonJr. grew up in Inglewood, Calif. -- geographically close but economically far from the Forum, where the Lakers played home games in front of Hollywood stars. Wigington couldn’t afford an NBA ticket, but he and his friends would play pickup basketball across the street on game days, knowing they would appear in TV shots of the arena.

“Where I lived, they called it the Bottom,” he says. “It is the lowest [point on the] economic totem pole in Southern California. Everybody was gangbanging in my neighborhood, but the really good athletes were protected.”

Wigington decided basketball was his way out, and his stature did not dissuade him. He saw his height as an asset: “I would take advantage of kids being off-balance, not knowing their center of gravity,” he says. Wigington became a top-ranked juco player at Ventura (Calif.) College, earned a scholarship to Seton Hall and eyed a pro career.

He studied accounting “so I could figure out how to count my money when I got to the NBA.” Then he tore up his right knee. After three surgeries, he had little cartilage left and no hope of playing in the pros.

Wigington, though, discovered that he had a flair for business. After graduating in 1990 with a degree in marketing, he invested in a dry cleaner and a few other ventures. But where he seemed to have a genuine soft touch was in entertainment and promotion. He launched a sports-marketing company out of South Orange, N.J., in ’95, taking on a few NBA players such as Rod Strickland and Cedric Ceballos. And he created other promotional and charitable events related to basketball too, working with an expanded circle of famous names. That brought him into the world of comedy -- a place where Wigington felt right at home.

Even 6-foot Sherman Douglas of Syracuse (left) towered over Wigington.

In 1999 he launched a comedy showcase on Hollywood’s Sunset Strip called Chocolate Sundaes, astutely letting young comedians into his shows for free. With Chocolate Sundaes, he says, he “built a brand versus building a show,” so that if talent left, he could replace it and keep rolling. (Wigington has since repackaged the stand-up showcase into the Showtime series of the same name.) Whenever he made money, Wigington put it in real estate.

Wigington does not assist his comedians with material, though he has two writers who sometimes help them punch it up. (“That’s not my lane,” he says.) His talent is not creating comedy, but identifying it and marketing it. Besides the 35-year-old Hart, Wigington has promoted successful comics DeRay Davis, Aries Spears, Katt Williams and Chris Spencer. And with some of his comics, he took on the role of financial adviser. “No matter how funny you are, not only do you have to pay your taxes, but you also have to set up your brand and business structure properly,” Wigington says. “You have to do all the things it takes to run a business, even though you’re the talent.”

Wigington doesn’t know how he got his ability to identify comedic talent but says, “I can look at a comic and listen to his act and his cadence onstage, and tell you if that kid has written or if he is stealing somebody’s stand-up. I can tell if he knows how to write by listening to five minutes of his material.”

When he first saw Hart perform during a Chocolate Sundaes show a dozen years ago, Wigington says, “he wasn’t experienced in the world, so it was very limited. But he understood who he was and became able to be self-deprecating in a way that the material was relevant to everyone.”

With Hart, Wigington says, “we worked together to get him to a place where he can do his work freely and not worry about what his financial situation looked like.” In 2005, Wigington helped the rising star set up a company, Hartbeat Productions, and became its vice president. Wigington shared an executive producer credit with Hart on the comedian’s 2013 stand-up movie, Kevin Hart: Let Me Explain, which grossed $32 million -- as well as on his 2011 film, Laugh at My Pain. Both movies are in Box Office Mojo’s list of the top 10 grossing stand-up comedy concerts.

Hart now has more than 12 million Twitter followers and is a fixture in show business, having appeared in such movies as Ride Along and Think Like a Man. He is a huge success story, and in his own way, so is Wigington, who now lives in California’s San Fernando Valley. In his free time, he coaches his four sons -- Leland III, Lathan, Landon and Lofton, who go by (in order) Snookey, Tookey, Wookey and Zookey -- in the game he knows and loves so well.

And if the kid from Inglewood wants to go to a Lakers game now, he has the connections and money to sit with the stars. He can settle into a courtside seat, knowing he rose from the Bottom to the top.

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